Sodium Methoxide → HCID 67852967, compound

HRID 1196375Notes

Reaction equation

HRID 1196375 reaction equation
[CH3:1][C:2]1([CH3:44])[CH2:7][O:6][CH:5]([CH:8]([C@@H:10]2[C@:27]3([CH3:28])[C@H:13]([C@H:14]4[C@H:24]([CH2:25][CH2:26]3)[C@:22]3([CH3:23])[C:17]([CH2:18][C@@H:19]([O:34]C(OC)=O)[CH2:20][C@@H:21]3[O:29]C(OC)=O)=[CH:16][CH:15]4[O:39]C(OC)=O)[CH2:12][CH2:11]2)[CH3:9])[O:4][CH2:3]1.C[O-].[Na+]>CO.O>[CH3:44][C:2]1([CH3:1])[CH2:3][O:4][CH:5]([CH:8]([C@@H:10]2[C@:27]3([CH3:28])[C@H:13]([C@H:14]4[C@H:24]([CH2:25][CH2:26]3)[C@:22]3([CH3:23])[C:17]([CH2:18][C@@H:19]([OH:34])[CH2:20][C@@H:21]3[OH:29])=[CH:16][C@H:15]4[OH:39])[CH2:12][CH2:11]2)[CH3:9])[O:6][CH2:7]1

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 67918793HCID 67918793, compound

Product 1

HCID 67852967HCID 67852967, compoundYield 90.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

In 5 ml of methanol was dissolved 100 mg of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,3β,7-tris(methoxycarbonyloxy)pregn-5-ene, followed by addition of 30 mg of sodium methoxide, and the mixture was stirred at room temperature for 5 hours. The reaction mixture was poured in water and extracted with methylene chloride. The extracts were pooled, washed with aqueous sodium chloride solution and concentrated under reduced pressure. The concentrate was recrystallized from ethyl acetate to give 65 mg of 20-(5,5-dimethyl-1,3-dioxan-2-yl)pregn-5-ene-1α,3β,7α-triol showing the following physical properties.

Workup

  1. extractionextracted with methylene chloride
  2. washwashed with aqueous sodium chloride solution
  3. concentrationconcentrated under reduced pressure
  4. customThe concentrate was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-4df465bf70bc40cfaa1c52a487faf14f
Source dataset
uspto-grants-1992_05
Patent number
US05112998

Reaction notes

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